Differentiation between Lutein Monoester Regioisomers and Detection of Lutein Diesters from Marigold Flowers (Tagetes erecta L.) and Several Fruits by Liquid Chromatography−Mass Spectrometry

Liquid chromatography−atmospheric pressure chemical ionization mass spectrometry (LC-APCIMS) was employed for the identification of eight lutein monoesters, formed by incomplete enzymatic saponification of lutein diesters of marigold (Tagetes erecta L.) by Candida rugosa lipase. Additionally, the ma...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2002-01, Vol.50 (1), p.66-70
Main Authors: Breithaupt, Dietmar E, Wirt, Ursula, Bamedi, Ameneh
Format: Article
Language:English
Subjects:
Agronomy. Soil science and plant productions
Asteraceae - chemistry
Biological and medical sciences
Chromatography, Liquid - methods
Economic plant physiology
Esters
Food additives
Food industries
Fruit - chemistry
Fundamental and applied biological sciences. Psychology
General aspects
Isomerism
Lutein - analysis
Mass Spectrometry - methods
Nutrition. Photosynthesis. Respiration. Metabolism
Plant Extracts - chemistry
Reserves and secretions. Pigments. Phytochromes
Sensitivity and Specificity
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Summary:Liquid chromatography−atmospheric pressure chemical ionization mass spectrometry (LC-APCIMS) was employed for the identification of eight lutein monoesters, formed by incomplete enzymatic saponification of lutein diesters of marigold (Tagetes erecta L.) by Candida rugosa lipase. Additionally, the main lutein diesters naturally occurring in marigold oleoresin were chromatographically separated and identified. The LC-MS method allows for characterization of lutein diesters occurring as minor components in several fruits; this was demonstrated by analysis of extracts of cape gooseberry (Physalis peruviana L.), kiwano (Cucumis metuliferus E. Mey. ex Naud.), and pumpkin (Cucurbita pepo L.). The assignment of the regioisomers of lutein monoesters is based on the characteristic fragmentation pattern:  the most intense daughter ion generally results from the loss of the substituent (fatty acid or hydroxyl group) bound to the ε-ionone ring, yielding an allylic cation. The limit of detection was estimated at 0.5 μg/mL with lutein dimyristate as reference compound. This method provides a useful tool to obtain further insight into the biochemical reactions leading to lutein ester formation in plants. Keywords: LC-MS; carotenoids; regioisomers; lutein monoester
ISSN:0021-8561
1520-5118
DOI:10.1021/jf010970l